Sailing

A must do while in Key West is some Key West Sailing! Join us with our professional crew and take to the waters of Key West. Let our crew dazzle you with their skills of sailing our yacht and taking care of you with the up most hospitality. Sailing is fun, but sailing and sightseeing is the most magical way to experience this Island of wonder. Enjoy a Key West Sunset Sail or Sail past Mallory Square, and cruise by Fort Zachary Taylor. Allow the dolphins to take your breath away on our Key West Day Sail and enjoy the excitement and art of Key West sailing. While sailing aboard the 105 foot Schooner America 2.0 you will experience the most premium sailing. This stunning classic boat was designed for comfort and speed. You will enjoy your time with us snapping photos, sipping on Champagne and cutting through the emerald green waters of Key West.

Sunset Sail aboard Schooner America 2.0

Enjoy your classic Key West sunset sail aboard the most elegant sailboat, the 105-foot, 1851 revival, Schooner America 2.0. Take in the vibrant colors of Key West’s famous sunset as you sip champagne, dine on passed hors d’oeurves, and glide through the crystal clear surrounding waters. This two-hour Key West sunset sail features complimentary champagne, wine, beer, soft drinks, and water. Passed hors d’oeurves are provided, including shrimp cocktail, a cheese plate, and delicious veggies! Schooner America 2.0 is a state of the art vessel built in 2011. She features teak decks, mahogany-trimmings, and 3600 square feet of canvas! Sit back and relax while she plies effortlessly through the turquoise green Key West sailing waters and off towards the horizon for the quintessential Key West Sunset experience!

Champagne & Aphrodisiacs Valentine’s Day Sail

This Valentine’s Day, take to the water and fall in love all over again. Join Schooner America 2.0 on a Key West Valentine’s Day Sunset Sail for an unforgettable sunset that is sure to tickle your taste buds and create a memory to last a lifetime. Celebrate this Valentine’s Day with your special someone on our Champagne and Aphrodisiacs Pairing Sunset Sail in Key West. As you sail along the beautiful turquoise green waters on the Schooner America 2.0, you and your loved one will be able to take in all the romance that this Key West Valentine’s Day Sunset Sail has to offer while being treated to a delicious pairing menu that is sure to entice consisting of hors d’ oeuvres expertly paired with champagnes and sparkling wines from around the world!

Classic Day Sail aboard Schooner America 2.0

Soak in the sun while you do some Key West Day Sailing! Take to the water on the Schooner America 2.0, named for the first boat to win the America’s Cup in 1851 for some Key West day sailing. This stunning 105-foot boat features teak decks, mahogany trimmings and ample seating. Her 3,600 square feet of sail will propel you smoothly through the crystal green waters of Key West Florida. This 1.5 hour Key West day sail features complimentary beer, wine, champagne and soft drinks! Refreshing fresh fruit is provided, but guests are encouraged to make the most of the event by bringing aboard their own picnic lunch!

Wreckers Race aboard Schooner America 2.0

All hands on deck join us for the Key West Wreckers Race! Sail aboard the Schooner America 2.0 for the monthly Schooner Wharf Bar Wrecker’s Race! Back in the days of the yore, pirate ships from afar often ran aground on Sand Key Reef, nine miles off of the southern coast of Key West. When all the scallywags in Key West heard there was booty to be had, they’d get in their boats and race each other out to the reef. The first one there could claim the ship’s cargo! Arrggh! Today, we celebrate it with the firing of the canon at 1:00pm to start the Key West Wreckers Race, and all of the schooners of are on their way in a one-way race to Sand Key Lighthouse! The boat that gets there first, “wins”! Enjoy the excitement aboard Schooner America 2.0 as we race for victory! An awards ceremony takes place at 9 PM at Schooner Wharf Bar where the winners are announced and treasures collected.

Full Moon Sail Aboard Schooner America 2.0

A Key West Full Moon Sail is sure to take your breath away. Take to the Key West waters by Full Moon Light!! This romantic, moonlight sailing adventure is yours aboard Key West’s most stunning sailboat, the 105-foot wooden schooner, America 2.0. America 2.0 features teak decks, mahogany-trimmings, and just under 3600 square feet of canvas! Sit back and relax on this Key West Full Moon Sail while she slices through the evening, basking in the golden moonlight that dances in the night waters. This special sail features complimentary beer, wine, champagne, soda, and water. Guests are encouraged to make the most of the event by bringing aboard their own picnic!

Key West Classic Regatta

The Key West Classic Regatta is designed after the Great Chesapeake Bay Schooner race and is a great way to see some of the most beautiful Key West schooners in their element. It is time to jump aboard and take an adventure on Key West’s most stunning sailboat, the 105-foot Schooner America 2.0 and be a part of this annual festivity! So, all hands on deck! Join us as we push off the dock at 10:30 AM for race start! America 2.0 features beautiful teak decks, mahogany-trimmings, and with 3,600 square feet of canvas, she flys! Sit back and relax while she plies effortlessly through the crystal Green Key West sailing waters towards the finish line!

Lighted Boat Parade aboard Schooner America 2.0

Join us for Key West Lighted Boat Parade, a favorite maritime holiday event. Sit aboard the fastest, most elegant schooner, the brand new eco-friendly, America 2.0 as we parade through the Bight and Harbor of Key West! She’ll be fully decorated in Holiday decor with up to 30 other Key West vessels in the annual Key West Lighted Boat Parade. Cruise aboard America 2.0 while taking in this magical display of holiday spirit. All of these vessels will have the opportunity to show off their creative and imaginative holiday decorations as they glide by the viewers and judges at the Schooner Wharf Bar.

New Year’s Eve Bash aboard Schooner America 2.0

Join us aboard America 2.0 for a wonderful New Year’s Eve Bash! This Key West New Year’s Eve Event aboard the Schooner America 2.0 is one that must not be missed. Enjoy this timeless celebration on the most exclusive boat in the Historic Bight, and experience VIP dockside access to the famous Schooner Wharf Bar “Lowering of the Pirate Wench” from the rig of Schooner America 2.0! This special ’21 and older’ event features complimentary beer, wine, champagne, well drinks, soda, water, and delicious hors d’ oeuvres! The Key West New Year’s Eve Event will separate you from the crowds and give you the best seat in the house for a front row viewing of the Lowering of the Pirate Wench.

Quantum Key West Race Week Spectator Sail aboard Schooner America 2.0

Join us on America 2.0, the Official Spectator Vessel for the 2017 Quantum Key West Race Week! This exciting event happens every year in these emerald green waters and you are going to have the best seat in the house. This is a week of sailing excitement that you do not want to miss out on. Schooner America 2.0 is a 105-foot schooner that has over 3600 square feet of sail, and a cutting edge free standing carbon fiber rig! With comfortable wrap around seating you are sure enjoy a afternoon in the sun for the Quantum Key West Race Week Spectator Sail on Schooner America 2.0!

SEE OUR CALENDAR OF EVENTS

PRIVATE YACHT CHARTERS

Sail out into the emerald green waters of Key West and impress your guests. Step aboard the legendary Schooner America 2.0 for a private charter. This yacht is perfect for Corporate outings, Birthdays, Anniversaries, Weddings, Team Building and more. Read more »

PUBLIC EVENTS

Sail out into NY Harbor and impress your guests. Step aboard one of our classic vessels for a private charter. These yachts are perfect for Corporate outings, Birthdays, Anniversaries, Weddings, Team Building and more. Read more »